The Matrons of Regal Bay

The Matrons of Regal Bay

Chapter 4

Annie's Tales -- Part 1

For Annie Strauss, her Wednesday started out quite promising. She awoke refreshed after a long, deep slumber. Rolling out of bed naked, she pulled on her Nike sweat suit in anticipation of an energetic morning jog through the neighborhood. After stopping off to brush her teeth, she headed to the kitchen for a light breakfast and a cup of coffee. As she stood at the counter preparing her coffee, Tim slipped up behind her and as he often did, he pressed up tight behind her, wrapping his arms around her waist.

"Morning, Annie," he purred into her ear, followed by a kiss on her long neck.

"Good morning, Tim," she responded. She felt his hips press forward into her buttocks, and the bulge of his "morning wood" press into the crack of her ass. Tim's right hand slipped downward across her flat belly and into the Y of her crotch to cup her pubic mound through the material of the sweat pants. Annie had yet to dress for work, and with the late start she always had on Wednesday, she still had plenty of time before she had to report in to the office. This was a fact that Tim was well aware of.

"You want some coffee?" she asked over her shoulder as he began to nuzzle her neck.

"I want a little something-something," Tim whispered into her ear. "And it isn't coffee."

Tim kissed along Annie's neckline for a moment as she wiggled her hips seductively against him. She was feeling a similar morning desire in her loins. When she turned to face Tim, his mouth went to hers, and as they kissed deeply, her hands went to his groin. Indeed, Tim was solidly ready for some morning action.

Annie was his MILF, as he sometimes referred to her. At 43, she was twenty-one years older than him, closer to twenty-two. Yet at this point in her life Annie was as energetic as any woman Tim's own age. She reached between their bodies past the top of the shorts he wore and found his cock. It was warm and rock-hard in her grip. She stroked along its length lightly, and then as she gripped his bulge, Tim moaned lustfully into her mouth. Annie tugged the elastic band of his own running shorts, loosening them around his waist, and then pushed downward. As they fell to the floor around his ankles, she followed right along, pulling his dark underwear along with her until his cock sprang out invitingly.

"I see you don't need any caffeine to get my favorite little man running," she grinned up at Tim while she wrapped her fingers around his manhood. Annie began to lick along the bottom of her lover's long cock. Tim combed his fingers through her curly, short red hair as she mouthed his cock from base to tip, and then, when her mouth wrapped around his knob, he moaned with greater pleasure. His cock heated rapidly within Annie's warm, wet mouth, and the dancing her tongue did around and across his knob had him raring to go.

Over the last few months, Annie had grown to be an expert cock-sucker, thanks in no small part to her young lover, who actually helped her learn how to deep-throat a dick. His was the first she'd ever fully taken willingly, and since then Annie had never failed to take his entire length down her throat each and every time she sucked him. That morning, kneeling before Tim in her kitchen, Annie eagerly sucked his cock right down into her gullet. With his balls pressed against her chin, her jaws wedged wide by his girth, Annie wiggled her tongue against the bottom of Tim's shaft for a moment before slipping her mouth back, her lips tight around his flesh, until only his knob remained inside. She breathed deeply though her nose and then went back down his shaft, again throating him fully. Back and forth Annie went, until Tim's cock was at its hardest and fullest.

"Jeezus, Mom!" Tim gulped. "That's so fucking good!"

Annie let his cock slip from her lips and smiled up at her twenty-two year-old son. "You like that, don't you?"

"Oh, hell yes!" he replied. He pulled her head back towards his crotch and as her jaw dropped he stuffed his cock into his mother's mouth once again. Annie worked his cock for a few more seconds before Tim began to pull at her shoulders. She gave his knob one last kiss and then stood.

"Turn around, Mom," Tim muttered even as he twisted Annie back to face the counter. Tim quickly pulled at the back of her sweat pants, exposing her skinny, pale ass. He tugged the narrow band of her red g-string underwear out of her crack and to the side. With her saliva coating his cock for lubrication, Tim bent at the knees to align himself with her sex. He took hold of his shaft and aimed into the dark crease of his mother's cunt. Annie bent forward, pushing the empty coffee cup aside, as Tim pushed his full length into her vagina from behind.

"Aaaahhh, Tim!" she moaned as his cock spread her labia and powered up through her vaginal chute. Her thighs, limited by how far they could spread apart by the sweat pants wrapped around her ankles, pressed back against Tim's as he bottomed out inside her.

"Oooohhh, Mom!" Tim echoed as his cock nudged against her cervix with his second thrust. He was as deep as he could go now, and with a firm hold of his mother's slim hips, Tim began to fuck his willing mother with hard thrusts.

"Oh, yeah, fuck me, Tim! Fuck me," Annie gasped. Her son's fat cock worked in and out of her smoothly, its familiar ridges and bumps tickling her in all of the right places. His knob banged against her deepest walls. Since they had started their affair some years back, her uterus was well protected by a regimen of birth-control pills. Since Annie loved nothing more than the feel of her son's hot cream bathing her womb upon his release, she never demanded he use a condom.

These early day screws were for him and his needs, and it wouldn't be long before Tim dumped that first thick load inside her belly. Annie rarely got off fully when Tim took her like this, although she often experienced micro-orgasms, as she called them, each time Tim entered her, and this morning was no exception. As her pussy trembled excitedly through a series of tiny climaxes, her juices flowed to coat Tim's dick and providing more than enough lubrication.

Tim reached out and under his mother's t-shirt and cupped her small breasts in his hands. His hips slammed forward against her ass, their flesh slapping together and echoing in the kitchen louder with every thrust.

"Ooohh, Mom! So good," Tim moaned. His hips slammed harder with every thrust against her tight, slim ass.

"Aaahh, yes, yes, yes," Annie grunted in time with his thrusts. Her head hung down and she looked between her parted thighs to see his hairy, heavy balls swinging. He was fired up and wouldn't last long, she recognized. Not like last night, she mused.

"Aaahh, Mom! I'm cumming!" Tim growled seconds later. He'd only been inside his mother's warm body for a few minutes, but such was the sensitivity his cock had each morning, Tim had little to no control over his release. His cock pulsed and spit its thick load into his mother's belly, coating her womb with his potent semen. He pulled Annie's hips back tight against his waist, holding his throbbing cock deep inside his mother, until a final pulse raced up his shaft and spit out the last drops of cream.

"So good," Tim sighed, working his cock slowly inside her for a few additional moments after his release. His balls relaxed and hung between his thighs and Annie reached between her thighs to allow her fingers to lightly stroke them, tickling him playfully.

Finally, Tim's cock began to relax and he stumbled back. His cock pulled free of his mother's strong vaginal grip with a plop and slapped wetly against his thigh. He pulled his underwear and shorts up, and began to draw the string tight once again. He wanted to have his mother's cream drying around his cock through the day.

Unknown to his mother/lover, Tim had another morning session already planned. Mrs. Coleman would be waiting for his visit, once her husband had left to drop their kids at school before heading on to his work up in the Majestic Mountains. Violet Coleman was a stay-at-home mom. Her husband David worked as a Crew Manager for the Cascade Lumber Company, and often spent days away, working the logging camps during the timber season. As a teenager, Tim had mowed the Coleman's lawn during the summers, just one of several he had in rotation. When her husband was away, she would sometime sunbathe as Tim worked. When she knew he was looking at her, she would slowly remove her top before rolling over onto her belly. Back then, she only teased him. These days, she provides a bit more than just a backyard tease. And Tim takes care of her other needs, little things that her husband didn't provide for her anymore. Violet wasn't ugly by any means, but she wasn't much of a looker anymore, even though she was only 36 years old. She was Korean-American, and her oval face was joined by an oval body after giving birth to her children. But it wasn't what she looked like that Tim enjoyed. It was what she did with what she had that drew him back to her, whenever she called.

Although their kitchen fuck had lasted less than ten minutes, Annie felt satisfied by her son's cock. Her pussy leaked cream and she pulled her tiny panties up to hold as much inside her as she could. Until she had to slip back into the shower and get ready for her day, that is. Annie enjoyed having his seed splashing around inside her when she made her morning jog. She imagined it gave her that little extra energy through the day that a 43-year-old woman needed.

"I love you, Mom," Tim told her as he grabbed a Monster energy drink from the refrigerator. He pulled her close and gave her a quick full-mouth kiss before heading towards his bedroom. She figured he was getting dressed for his day, though what he had planned she didn't know. Tim went out through the back door and a minute later she heard his motorcycle fire up.

For Annie, the rest of her day went as usual. Her run was peaceful and refreshing. Her day at work, even though it was her "short-day", was busy. Working for Natalya Aleshinova was always stressful, though never over-demanding of her. For the most part, her day was spent going over the events schedules for the next three weeks at the Golf Club. The Western States Senior Invitational was due to start in a week and final preparations were moving smoothly along. The only glitch in the plans came when the catering service informed them that an expected shipment of wine had yet to arrive, and the suggested list of substitutes had to be presented for approval to the Events Director, her aunt Gloria Van Winkle.

Annie was born Anne Van Winkle, daughter of Greta and Jonas Van Winkle. She was the older of two daughters, her sister Charlotte being three years younger than her. Annie had remained in Regal Bay after high school to attend the university on a liberal arts scholarship. However, Annie turned her attentions early on to William Strauss, Jr., a charming young man whom Annie fell for at first sight.

William, or Bill as he preferred, had come to Regal Bay from Boise to attend the university along with his sister, Ivy. Bill was a hard, young man who reminded Annie of the classic Marlboro Man advertising. They shared several classes her freshman year, although Bill was a year older than her. They soon became a couple. By the time they both were in their senior year, Bill had started interning at the Majestic County Times, the area's major newspaper. Bill had been taking journalism classes throughout school, and yet still hadn't decided to follow it as a career choice. Annie, who hadn't decided on a solid choice for a career, either, chose not to enroll in classes in what would have been her final semester. Instead, she and Bill got married and she chose instead to be his housewife.

Bill eventually did hire on at the paper, and even with Annie's family disapproving of her choice, they supported her. During these first years, Annie gave birth to their only child, Tim. Afterward, her doctors informed Annie and Bill that, due to complications following the birth, she would not be able to have any more children. Annie was devastated, and even though Bill seemed to take it in stride, he had wanted more than just one child from the outset. This flaw that he perceived in Annie eventually would lead to his becoming unfaithful to her.

As Tim grew and started school, Annie went to work at the Golf Club. She had discovered that she had a knack for organization and soon she was assigned to be Natalya Aleshinova's assistant. It was a position Annie enjoyed from the outset. Working long hours more nights than not contributed to her husband's infidelity, she realized afterward.

Eventually their marriage began to dissolve to the point the Bill often spent several nights away. At times he would stay with his sister, who worked downtown at the City Center for the Parks Department. Other times, Annie had no idea where he slept. Annie didn't think he was seeing anyone on the side, but she never found out one way or the other. On the way home from work, and after calling to let her know he wanted to talk over dinner, Bill's car was hit by a drunk driver in a dump truck while sitting at a red light. He was killed. At thirty years old, Annie was a widow, and eight-year-old Tim was fatherless.

Although Annie and her sister-in-law had never been close, or even friends, Ivy agreed to help take care of Tim while Annie worked to complete her Bachelor's degree by taking night courses. During these next half-dozen years, Annie had maintained a celibate life, a decision that would soon weigh heavily on her.

Annie eventually earned her Bachelor's degree in Business Management and began to seriously think about continuing her education towards a Master's. Now a forty year-old single mother, it was a degree that Annie had long hoped to attain, and with thanks to Ivy and her husband, Annie was able to earn her Master's degree during Tim's high school years.

It happened that during Tim's senior year at the high school, Annie suddenly began to dream about her son in a very inappropriate and sinful manner. Even though she recognized that she could not help how she dreamed, she did recognize the fact that she was beginning to see her son in a much different light afterward. Tim had grown to be a handsome young man by the time he was eighteen, at least in her eyes. Outwardly, Tim was tall and skinny, with a pitted, rugged complexion due to a severe case of the chicken pox as a child. He wore glasses and had only recently had his braces removed. He hung out with guys, whom many considered geeks, playing video games or talking about technical innovations most days.

Tim seldom talked about girls, at least around his mother. He was participating in the school's "work release" program and worked part-time at the Best Buy in the Majestic Mall after school three days a week. Upon graduation Tim was planning on working towards a degree in the Media Sciences, a new program at the School of Liberal Arts at Regal Bay University. As Annie had been told over dinner one evening, several of Tim's friends were also planning a similar course of study. Eventually Annie would come to understand why.

Life with Tim in her home had become stressful, as life with older teenagers often did. He wanted to do his own thing, come and go as he pleased, and lead a private life that didn't include his mother. For Annie, she felt lonely more often than not. It didn't help that, when she confided in her friends what she was going through, several suggested she get out and start playing the field. Annie was never one to hit the bars or clubs, although she did belong to the Golf Club's bowling league. If fact, it had been during a league night that, while enjoying beers, Annie was asked by her team-mate, Cynthia Price, if she'd ever had sexual feeling towards her son.

"Oh, my god! You have!" Cynthia declared, sensing the answer from Annie's hesitation in responding.

"No, I haven't!" Annie insisted. "I don't think about him like that," she maintained, but knew she was lying. She confessed, "I have been having dreams, however."

Cynthia, a Professor of Sociology at Regal Bay University, was well versed in sexual desires and deviances, having published several papers on the topics. Maternal Incest was of key interest to her, as Annie was soon to learn. Annie confessed a few of her dreams, though not going into detail, as their evening went on. By the time they had finished, Cynthia insisted that Annie join her for dinner some night soon, "To go into better detail and maybe even get to the root issue," Cynthia had explained.

Come Friday of that week, it was Tim's nineteenth birthday. He was in his freshman year at the university, though still living at home with his mother. Annie had made plans to take her son out to dinner to celebrate his birthday, but was unable to get out of work before six. In the meantime, Tim had been asked over to his Aunt Ivy's house that afternoon to celebrate his birthday. By the time Annie did get home well after seven in the evening, she found her son already at home, and just slightly drunk. He was in his room, tinkering around with a used lap top computer that he had picked up at one of the pawn shops. Annie immediately smelled the alcohol on him and demanded to know the story.

"Aunt Ivy was having a few drinks, and offered me a couple," he explained. "I'm okay, not drunk really, just feeling pretty good." His smile, however, was crooked and his eyes sparkled oddly as he looked at her.

"I really don't give a shit!" Annie barked. "Ivy is a bad influence on you. I'm going to call her right now and a give her a piece of my mind. I ought to call the police on her, you know. You're not old enough to drink at all!"

"Mom, don't, please," Tim pleaded. "It's okay, really. Sam and Leah and Parky were there, too. We all had a little to drink, to celebrate my birthday, you know. I wish you were there, too."

Annie stood looking at her son, tapping her foot on the floor. She was angry, with her sister-in-law and not her son, and knew she shouldn't take it out on him. Tim was close to his cousins and it had been good for him to celebrate with them.

"We're going out tomorrow night to celebrate, remember," she reminded him. "I've got reservations already. It will be nice, just the two of us."

"I remember, and I'm looking forward to it. A birthday date with my pretty mom, and who knows, I might even have fun," he added with a wide grin. It had always been a rub between them that they never had fun together, with her always working and him either in school or at work. They rarely got to spend any quality time together. This dinner "date" that Annie had set up would be the first time they had been out together in months.

"Well, I'm hoping we have fun as well," she told him. "I'm still not pleased with your Aunt getting you liquored up. You know how that hurts me."

Tim remembered then that his father had been killed by a drunk driver, and suddenly felt very bad. He went to his feet and took his mother in his arms. He was a good six-inches taller than her now, and it only just registered for both of them.

"I'm sorry, Mom, I wasn't thinking," Tim apologized. "I guess Aunt Ivy wasn't either."

"Your Aunt rarely thinks about others, Tim. She lives in the moment and cares little about how her actions and words might hurt others. Why do you think her husband left her? He got fed up with her shit, is why."

"Come on, Mom," Tim insisted. "Let it go, okay? I'll go take a shower and get cleaned up, and then we'll go out, okay?"

"I've got reservations for tomorrow night," she reminded.

"We'll just go get pizza, or maybe a steak?" he suggested. "It's my birthday, so let's do what I want, tonight at least. Tomorrow, you can give me your dinner-date as a present."